Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. 10111-08-7, formula is C4H4N2O, Name is 1H-Imidazole-2-carbaldehyde. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents. Safety of 1H-Imidazole-2-carbaldehyde.
Martin, Sebastian;Maus, Stephan;Stemler, Tobias;Rosar, Florian;Khreish, Fadi;Holland, Jason P.;Ezziddin, Samer;Bartholomae, Mark D. research published 《 Proof-of-Concept Study of the NOTI Chelating Platform: Preclinical Evaluation of 64Cu-Labeled Mono- and Trimeric c(RGDfK) Conjugates》, the research content is summarized as follows. We recently developed a chelating platform based on the macrocycle 1,4,7-triazacyclononane with up to three five-membered azaheterocyclic arms for the preparation of 68Ga- and 64Cu-based radiopharmaceuticals. Based on this platform, the chelator scaffold NOTI-TVA with three addnl. carboxylic acid groups for bioconjugation was synthesized and characterized. The primary aims of this proof-of-concept study were (1) to evaluate if trimeric radiotracers on the basis of the NOTI-TVA 6 scaffold can be developed, (2) to determine if the addnl. substituents for bioconjugation at the non-coordinating NH atoms of the imidazole residues of the building block NOTI influence the metal binding properties, and (3) what influence multiple targeting vectors have on the biol. performance of the radiotracer. The cyclic RGDfK peptide that specifically binds to the αvβ3 integrin receptor was selected as the biol. model system. Two different synthetic routes for the preparation of NOTI-TVA 6 were explored. Three c(RGDfK) peptide residues were conjugated to the NOTI-TVA 6 building block by standard peptide chem. providing the trimeric bioconjugate NOTI-TVA-c(RGDfK)39. Labeling of 9 with [64Cu]CuCl2 was performed manually at pH 8.2 at ambient temperature Binding affinities of Cu-8, the Cu2+ complex of the previously described monomer NODIA-Me-c(RGDfK) 8, and the trimer Cu-9 to integrin αvβ3 were determined in competitive cell binding experiments in the U-87MG cell line. The pharmacokinetics of both 64Cu-labeled conjugates [64Cu]Cu-8 and [64Cu]Cu-9 were determined by small-animal PET imaging and ex vivo biodistribution studies in mice bearing U-87MG xenografts. Depending on the synthetic route, NOTI-TVA 6 was obtained with an overall yield up to 58%. The bioconjugate 9 was prepared in 41% yield. Both conjugates [64Cu]Cu-8 and [64Cu]Cu-9 were radiolabeled quant. at ambient temperature in high molar activities of Am ∼ 20 MBq nmol-1 in less than 5 min. Competitive inhibitory constants IC50 of c(RDGfK) 7, Cu-8, and Cu-9 were determined to be 159.5 ± 1.3 nM, 256.1 ± 2.1 nM, and 99.5 ± 1.1 nM, resp. In small-animal experiments, both radiotracers specifically delineated αvβ3 integrin-pos. U-87MG tumors with low uptake in non-target organs and rapid blood clearance. The trimer [64Cu]Cu-9 showed a ∼ 2.5-fold higher tumor uptake compared with the monomer [64Cu]Cu-8. Functionalization of NOTI at the non-coordinating NH atoms of the imidazole residues for bioconjugation was straightforward and allowed the preparation of a homotrimeric RGD conjugate. After optimization of the synthesis, required building blocks to make NOTI-TVA 6 are now available on multi-gram scale. Modifications at the imidazole groups had no measurable impact on metal binding properties in vitro and in vivo suggesting that the NOTI scaffold is a promising candidate for the development of 64Cu-labeled multimeric/multifunctional radiotracers.
Safety of 1H-Imidazole-2-carbaldehyde, 1H-Imidazole-2-carbaldehyde, also known as 1H-Imidazole-2-carbaldehyde, is a useful research compound. Its molecular formula is C4H4N2O and its molecular weight is 96.09 g/mol. The purity is usually 95%.
1H-Imidazole-2-carboxaldehyde is a novel PTP1b inhibitor with potential application to treat type 2 diabetes.
1H-Imidazole-2-carboxaldehyde is a broad-spectrum antimicrobial that has been shown to inhibit the growth of bacteria by interfering with protein synthesis. It binds to the cytosolic protein and receptor molecule, which are involved in the activation of bacterial enzymes. Imidazole-2-carboxaldehyde reacts with anhydrous sodium and copper complex to produce hydrogen bonds, which prevent the formation of the nitrogen atoms necessary for cellular processes. This chemical also has biological properties such as glyoxal, which inhibits bacterial growth by reacting with amino groups on proteins., 10111-08-7.
Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem